“All This Time” by Tiffany (1988)

Once upon a time, in the ‘80s, there were two teenage girls who made pop music. Debbie Gibson was the wholesome girl from Long Island who played piano, listed Billy Joel and had a crush on George Michael-as did a lot of other woefully misguided teenage girls (and women) in that time period.

Tiffany was more of the wild card. She initially gained popularity due to a novel idea–mall tours. Hmmm…taking a teenage girl singer to a place where lots of other teenage girls hang out? WHAT A CONCEPT? She also dated Jonathan Knight for a period of time. So obviously it’s a thing for female pop singers to crush hard on gay fellas.

“All This Time” was the debut single from Tiffany’s second album. It’s the best song ever recorded by either of the two teen queens of the era. Musically, there’s not a ton going on. But Tiffany sings the shit out of this song, and not in a showy Christina Aguilera note-bendy kinda way either. Tiffany sang about heartbreak like she’d legitimately experienced it (which, considering she’d just legally emancipated herself from her mom, is quite plausible), and the spare instrumentation (all synths/drum machines minus one guitar solo) makes her vocal even more haunting. It was her last major hit, but damn, what a way to go out.

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